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Erschienen in: Journal of Polymer Research 9/2012

01.09.2012 | Original Paper

Synthesis of new unsymmetrical diamine and polyimides: structure–property relationship and applications of polyimides

verfasst von: P. Thiruvasagam

Erschienen in: Journal of Polymer Research | Ausgabe 9/2012

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Abstract

A novel unsymmetrical diamine monomer 4-(2-(4-(4-aminophenoxy)phenyl)propan-2-yl)benzenamine (APPBA) containing –O– and –C(CH3)– groups was synthesized from 2-(4-aminophenyl)-2-(4-hydroxyphenyl)propane and 4-nitrofluorobenzene by the nucleophilic substitution reaction followed by catalytic reduction. Polycondensation of this diamine with aromatic dianhydrides through thermal solution imidization techniques afford a series of novel processable polyimides (PI). The structure of the monomer and polyimides were confirmed by FT-IR and 1H-NMR. The polyimides were characterized by XRD, TGA, DSC, electrical property, solution viscosity and solubility test. These polyimides had inherent viscosities in the range 0.48–0.61 dL/g. The X-ray diffraction measurements indicated that all these polyimides were amorphous. The polyimides exhibited excellent solubility in most of the organic solvents. The glass transition temperature (Tg) was observed in the range 242–282 °C. The polyimides displayed good thermal stability and the temperatures at which 10 % weight loss occurred in the range 475–504 °C. The dielectric constant of PIs was in the range of 2.82–3.55.

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Literatur
1.
Zurück zum Zitat Tsai P-F, Chyong-Fen W, Hsiao Y-C, Shau M-D (2009) Properties of novel polyimides containing bismaleimide and cyclic phosphine oxide. J Polym Res 16:673–680CrossRef Tsai P-F, Chyong-Fen W, Hsiao Y-C, Shau M-D (2009) Properties of novel polyimides containing bismaleimide and cyclic phosphine oxide. J Polym Res 16:673–680CrossRef
2.
Zurück zum Zitat Fang X, Wang Z, Yang Z, Gao L, Li Q, Ding M (2003) Novel polyimides derived from 2,3,3′,4′-benzophenonetetracarboxylic dianhydride. Polymer 44:2641–2646CrossRef Fang X, Wang Z, Yang Z, Gao L, Li Q, Ding M (2003) Novel polyimides derived from 2,3,3′,4′-benzophenonetetracarboxylic dianhydride. Polymer 44:2641–2646CrossRef
3.
Zurück zum Zitat Mallakpour S, Tirgir F, Sabzalian MR (2011) Synthesis and structural characterization of novel biologically active and thermally stable poly(ester-imide)s containing different natural amino acids linkages. J Polym Res 18:373–384CrossRef Mallakpour S, Tirgir F, Sabzalian MR (2011) Synthesis and structural characterization of novel biologically active and thermally stable poly(ester-imide)s containing different natural amino acids linkages. J Polym Res 18:373–384CrossRef
4.
Zurück zum Zitat Vijay Kumar S, Yu H-C, Choi J, Kudo K, Jang Y-H, Chung C-M (2011) Structure–property relationships for partially aliphatic polyimides. J Polym Res 18:1111–1117CrossRef Vijay Kumar S, Yu H-C, Choi J, Kudo K, Jang Y-H, Chung C-M (2011) Structure–property relationships for partially aliphatic polyimides. J Polym Res 18:1111–1117CrossRef
5.
Zurück zum Zitat Perry RJ, Scott E, Tunny B, Wilson D (1996) Polyimides formation through the palladium-mediated carbonylation and coupling of Bis(o-iodo amides) and diamines. Macromolecules 29:1014–1020CrossRef Perry RJ, Scott E, Tunny B, Wilson D (1996) Polyimides formation through the palladium-mediated carbonylation and coupling of Bis(o-iodo amides) and diamines. Macromolecules 29:1014–1020CrossRef
6.
Zurück zum Zitat Hsiao S-H, Guo W, Kung Y-C, Lee Y-J (2011) Redox-active and electrochromic aromatic poly(amide-imide)s with 2,4-dimethoxytriphenylamine chromophores. J Polym Res 18:1353–1364CrossRef Hsiao S-H, Guo W, Kung Y-C, Lee Y-J (2011) Redox-active and electrochromic aromatic poly(amide-imide)s with 2,4-dimethoxytriphenylamine chromophores. J Polym Res 18:1353–1364CrossRef
7.
Zurück zum Zitat Yang CP, Su YY (2003) Properties of organosoluble aromatic polyimides from 3′-trifluoromethyl-3,4′-oxydianiline. Polymer 44:6311–6322CrossRef Yang CP, Su YY (2003) Properties of organosoluble aromatic polyimides from 3′-trifluoromethyl-3,4′-oxydianiline. Polymer 44:6311–6322CrossRef
8.
Zurück zum Zitat Seyed M, Amini N, Mousa G (2011) Synthesis and characterization of new polyamides and polyimides containing dioxypyrimidine moiety in the main chain with bulky imidazole pendent group: solubility, thermal and photophysical properties. J Polym Res 18:1575–1586CrossRef Seyed M, Amini N, Mousa G (2011) Synthesis and characterization of new polyamides and polyimides containing dioxypyrimidine moiety in the main chain with bulky imidazole pendent group: solubility, thermal and photophysical properties. J Polym Res 18:1575–1586CrossRef
9.
Zurück zum Zitat Ree M (2006) High performance polyimides for applications in microelectronics and flat panel displays. Macromol Res 14:1–33CrossRef Ree M (2006) High performance polyimides for applications in microelectronics and flat panel displays. Macromol Res 14:1–33CrossRef
10.
Zurück zum Zitat Koytepe S, Pasahan A, Ekinci E, Alıcı B, Seckin T (2008) Synthesis, characterization of phosphine oxide-containing polyimides and their use as selective membrane for dopamine. J Polym Res 15:249–257CrossRef Koytepe S, Pasahan A, Ekinci E, Alıcı B, Seckin T (2008) Synthesis, characterization of phosphine oxide-containing polyimides and their use as selective membrane for dopamine. J Polym Res 15:249–257CrossRef
11.
Zurück zum Zitat Thiruvasagam P, Venkatesan D (2009) Synthesis and characterization of polyetherimides derived from AB monomers. J Macromol Sci Pure Appl Chem 46:419–424CrossRef Thiruvasagam P, Venkatesan D (2009) Synthesis and characterization of polyetherimides derived from AB monomers. J Macromol Sci Pure Appl Chem 46:419–424CrossRef
12.
Zurück zum Zitat Thiruvasagam P, Vijayan M (2012) Synthesis of new diacid monomers and poly(amideimide)s: study of structure-property relationship and applications. J Polym Res 19:9845CrossRef Thiruvasagam P, Vijayan M (2012) Synthesis of new diacid monomers and poly(amideimide)s: study of structure-property relationship and applications. J Polym Res 19:9845CrossRef
13.
Zurück zum Zitat Thiruvasagam P, Shiva C, Sundararaman C, Venkatesan D (2011) Synthesis and characterization of new Diimide Diols and Processable Poly(esterimide)s derived there from. Polymer Polymer Compos 19:717–726 Thiruvasagam P, Shiva C, Sundararaman C, Venkatesan D (2011) Synthesis and characterization of new Diimide Diols and Processable Poly(esterimide)s derived there from. Polymer Polymer Compos 19:717–726
14.
Zurück zum Zitat Li Y, Wang Z, Li G, Ding M, Yan J (2012) Synthesis and properties of polyimides based on isomeric (4,4′-methylenediphenoxyl) bis(phthalic anhydride)s (BPFDAs). J Polym Res 19:9772CrossRef Li Y, Wang Z, Li G, Ding M, Yan J (2012) Synthesis and properties of polyimides based on isomeric (4,4′-methylenediphenoxyl) bis(phthalic anhydride)s (BPFDAs). J Polym Res 19:9772CrossRef
15.
Zurück zum Zitat Ghaemy M, Alizadeh R (2009) Synthesis of soluble and thermally stable polyimides from unsymmetrical diamine containing 2,4,5-triaryl imidazole pendent group. Eur Polym J 45:1681–1688CrossRef Ghaemy M, Alizadeh R (2009) Synthesis of soluble and thermally stable polyimides from unsymmetrical diamine containing 2,4,5-triaryl imidazole pendent group. Eur Polym J 45:1681–1688CrossRef
16.
Zurück zum Zitat Thiruvasagam P, Venkatesan D (2010) Synthesis and characterization of processable aromatic polyimides. High Perform Polymer 22:682–693CrossRef Thiruvasagam P, Venkatesan D (2010) Synthesis and characterization of processable aromatic polyimides. High Perform Polymer 22:682–693CrossRef
17.
Zurück zum Zitat Saeed Butt M, Akhter Z, Zafar-uz-Zaman M, Siddiqi HM (2008) Synthesis and characterization of some Schiff-base-containing polyimides. Colloid Polym Sci 286:1455–1461CrossRef Saeed Butt M, Akhter Z, Zafar-uz-Zaman M, Siddiqi HM (2008) Synthesis and characterization of some Schiff-base-containing polyimides. Colloid Polym Sci 286:1455–1461CrossRef
18.
Zurück zum Zitat Thiruvasagam P, Venkatesan D (2011) Synthesis and characterization of polyetherimides via nitrodisplacement reaction. High Perform Polymer 23:22–31 Thiruvasagam P, Venkatesan D (2011) Synthesis and characterization of polyetherimides via nitrodisplacement reaction. High Perform Polymer 23:22–31
19.
Zurück zum Zitat Nasab SMA, Ghaemy M (2011) Synthesis and characterization of new polyamides and polyimides containing dioxypyrimidine moiety in the main chain with bulky imidazole pendent group:solubility, thermal and photophysical properties. J Polym Res 18:1575–1586CrossRef Nasab SMA, Ghaemy M (2011) Synthesis and characterization of new polyamides and polyimides containing dioxypyrimidine moiety in the main chain with bulky imidazole pendent group:solubility, thermal and photophysical properties. J Polym Res 18:1575–1586CrossRef
20.
Zurück zum Zitat Zhang S-J, Li Y-F, Wang X-L, Zhao X, Shao Y, Ma T (2007) Synthesis and characterization of soluble polyimides derived from the polycondensation of 2, 6-bis (4-amino-2- trifluoromethylphenoxy-4′-benzoyl)pyridine with some aromatic dianhydrides. High Perform Polymer 19:462–476CrossRef Zhang S-J, Li Y-F, Wang X-L, Zhao X, Shao Y, Ma T (2007) Synthesis and characterization of soluble polyimides derived from the polycondensation of 2, 6-bis (4-amino-2- trifluoromethylphenoxy-4′-benzoyl)pyridine with some aromatic dianhydrides. High Perform Polymer 19:462–476CrossRef
21.
Zurück zum Zitat Chen J-C, Rajendran K, Huang S-W, Chang H-W (2011) Synthesis and characterization of aromatic polyamides derived from various derivatives of 4,4′-oxydianiline. J Polym Res 18:1693–1703CrossRef Chen J-C, Rajendran K, Huang S-W, Chang H-W (2011) Synthesis and characterization of aromatic polyamides derived from various derivatives of 4,4′-oxydianiline. J Polym Res 18:1693–1703CrossRef
22.
Zurück zum Zitat Chern Y-T, Twua J-T, Chen J-C (2009) High Tg and high organosolubility of novel polyimides containing twisted structures derived from 4-(4-amino-2-chlorophenyl)-1-(4-aminophenoxy)-2,6-di-tert-butylbenzene. Eur Polym J 45:1127–1138CrossRef Chern Y-T, Twua J-T, Chen J-C (2009) High Tg and high organosolubility of novel polyimides containing twisted structures derived from 4-(4-amino-2-chlorophenyl)-1-(4-aminophenoxy)-2,6-di-tert-butylbenzene. Eur Polym J 45:1127–1138CrossRef
23.
Zurück zum Zitat Kim YP, Glass TE, Lyle GD, Mcgrath JE (1993) kinetics and mechanistic investigation of the formation of polyimides under homogeneous conditions. Macromolecules 36:1354–1358 Kim YP, Glass TE, Lyle GD, Mcgrath JE (1993) kinetics and mechanistic investigation of the formation of polyimides under homogeneous conditions. Macromolecules 36:1354–1358
24.
Zurück zum Zitat Yilmaz T, Guclu H, Ozarslan O, Yildiz E, Kuyulu A, Ekinci E, Gungor A (1997) Kinetic investigations of formation of polyimides containing arylene sulfone ether linkages by potentiometric titration and their characterization. Polym Sci Part A Polym Chem 35:2981–2990CrossRef Yilmaz T, Guclu H, Ozarslan O, Yildiz E, Kuyulu A, Ekinci E, Gungor A (1997) Kinetic investigations of formation of polyimides containing arylene sulfone ether linkages by potentiometric titration and their characterization. Polym Sci Part A Polym Chem 35:2981–2990CrossRef
25.
Zurück zum Zitat Mallakpour S, Soltanian S, Sabzalian MR (2011) Studies on synthesis and in vitro biodegradability of novel optically active nanostructure poly(ester-imide)s containing L-phenylalanine and L-isoleucine linkages. Colloid Polym Sci 289:93–100CrossRef Mallakpour S, Soltanian S, Sabzalian MR (2011) Studies on synthesis and in vitro biodegradability of novel optically active nanostructure poly(ester-imide)s containing L-phenylalanine and L-isoleucine linkages. Colloid Polym Sci 289:93–100CrossRef
26.
Zurück zum Zitat Khalil F, Mohsen H, Meisam S (2010) New photosensitive and optically active organo-soluble poly(amide–imide)s from N, N′-(bicyclo[2, 2, 2]oct-7-enetetra carboxylic)-bis-L-amino acids and 1,5-bis(4-aminophenyl)penta-1,4-dien-3-one: synthesis and characterization. J Polym Res 17:379–390CrossRef Khalil F, Mohsen H, Meisam S (2010) New photosensitive and optically active organo-soluble poly(amide–imide)s from N, N′-(bicyclo[2, 2, 2]oct-7-enetetra carboxylic)-bis-L-amino acids and 1,5-bis(4-aminophenyl)penta-1,4-dien-3-one: synthesis and characterization. J Polym Res 17:379–390CrossRef
27.
Zurück zum Zitat Yang C-P, Chen Y-C, Hsiao S-H, Guo W, Wang H-M (2010) Optically transparent and colorless poly(ether-imide)s derived from a phenylhydroquinone bis(ether anhydride) and various trifluoromethyl-substituted bis(ether amine)s. J Polym Res 17:779–788CrossRef Yang C-P, Chen Y-C, Hsiao S-H, Guo W, Wang H-M (2010) Optically transparent and colorless poly(ether-imide)s derived from a phenylhydroquinone bis(ether anhydride) and various trifluoromethyl-substituted bis(ether amine)s. J Polym Res 17:779–788CrossRef
28.
Zurück zum Zitat Purushothaman R, Mohammed Bilal I, Palanichamy M (2011) Effect of chemical structure of aromatic dianhydrides on the thermal, mechanical and electrical properties of their terpolyimides with 4,4′-oxydianiline. J Polym Res 18:1597–1604CrossRef Purushothaman R, Mohammed Bilal I, Palanichamy M (2011) Effect of chemical structure of aromatic dianhydrides on the thermal, mechanical and electrical properties of their terpolyimides with 4,4′-oxydianiline. J Polym Res 18:1597–1604CrossRef
Metadaten
Titel
Synthesis of new unsymmetrical diamine and polyimides: structure–property relationship and applications of polyimides
verfasst von
P. Thiruvasagam
Publikationsdatum
01.09.2012
Verlag
Springer Netherlands
Erschienen in
Journal of Polymer Research / Ausgabe 9/2012
Print ISSN: 1022-9760
Elektronische ISSN: 1572-8935
DOI
https://doi.org/10.1007/s10965-012-9965-7

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